Synthesis and characterization of benzothiazol-2-one derivatives as anti-inflammatory and analgesic agents

A series of new compounds bearing a 1,3-benzothiazol-2-one nucleus have been synthesized using 5,6-dimethyl-3-(2-oxo-propyl)-1,3-benzothiazol-2-one (1) as a key starting compound. The reaction of 1 with some nucleophilic compounds led to the formation of compounds 2, 3, 4, 5a, b, 6 and 7a, b. The thiosemicarbazone derivatives 7a, b were treated with a number of halo ketones to produce the new heterocyclic compounds 9-13, while their reaction with acid anhydrides led to the formation of the derivatives 14 and 15. Also, compound 1 was condensed with different aromatic aldehydes to afford the corresponding chalcones 18-22. The structures of all the novel compounds have been determined by analytical and spectral data. Some of the compounds were selected to be evaluated as anti-inflammatory and analgesic agents.